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| 2/20/2021 | Southern Raceway - Milton, FL USCS Battle at the Beach Winter Nationals Round #1 360 Sprints - Winged: USCS United Sprint Car Series Midgets: POWRi Economy Midgets: POWRi Outlaw Midgets Stock Cars, Sportsmans, Winged A-Class, CRUSA Street Stocks, Pure Stock | Results | | Henry Bailey (Pure Stock) | 2nd | - | - | 3rd |
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| 2/21/2021 | Southern Raceway - Milton, FL Battle at the Beach (Night 2) 360 Sprints - Winged: USCS United Sprint Car Series Midgets, Economy Midgets, Winged A-Class, Vintage Full Body Stock Cars, Hornets, Junior Slingshots | Results | | Henry Bailey (Vintage Full Body Stock Cars) | 3rd | - | - | 5th |
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| 3/12/2021 | Southern Raceway - Milton, FL Spring Break Bash (Night 1) Dirt Super Late Models: Southern All Stars DIRTcar UMP Modifieds, Vintage Full Body Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock, Junior Slingshots | Results | | Henry Bailey (Vintage Full Body Stock Cars) | 6th | - | - | - |
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| 3/13/2021 | Southern Raceway - Milton, FL Dirt Super Late Models: Southern All Stars DIRTcar UMP Modifieds, Stock Cars, Vintage Full Body Stock Cars, Non Wing Crate Sprints, CRUSA Street Stocks, Pure Stock | Results | | Henry Bailey (Vintage Full Body Stock Cars) | - | - | - | 17th |
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| 3/27/2021 | Southern Raceway - Milton, FL Season Opener Hobby Stocks, Stock Cars, B Modifieds, Vintage Full Body Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock | Results | | Henry Bailey (Pure Stock) | 3rd | - | - | 9th |
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| 5/15/2021 | Southern Raceway - Milton, FL USCS Salute to Armed Forces Weekend Round #2 360 Sprints - Winged: USCS United Sprint Car Series Sportsmans, Winged A-Class, Vintage Full Body Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock | Results | | Henry Bailey (Pure Stock) | 3rd | - | - | 10th |
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| 9/5/2021 | Southern Raceway - Milton, FL Deep Southern Shine Run Factory Stocks, B Modifieds, Vintage Full Body Stock Cars, Hornets, CRUSA Street Stocks, CRUSA Dirt Late Models, Pure Stock | Results | | Henry Bailey (Pure Stock) | 2nd | - | - | 3rd |
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| 9/25/2021 | Southern Raceway - Milton, FL Regular Racing B Modifieds, Vintage Full Body Stock Cars, Hornets, CRUSA Dirt Late Models, Pure Stock | Results | | Henry Bailey (Pure Stock) | 2nd | - | - | 2nd |
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| 10/9/2021 | Southern Raceway - Milton, FL Doug Merritt Memorial Demolition Derby Stock Cars, Vintage Full Body Stock Cars, Hornets, CRUSA Street Stocks, CRUSA Dirt Late Models, Pure Stock | Results | | Henry Bailey (Pure Stock) | 2nd | - | - | 4th |
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| 10/23/2021 | Southern Raceway - Milton, FL Season Championship Stock Cars, Sportsmans, Vintage Full Body Stock Cars, Hornets, Non Wing Crate Sprints, CRUSA Street Stocks, Pure Stock | Results | | Henry Bailey (CRUSA Street Stocks) | - | - | - | 5th | | Henry Bailey (Pure Stock) | - | - | - | 5th |
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| 11/19/2021 | Southern Raceway - Milton, FL King of the Sandbox Friday Night Dirt Super Late Models, Stock Cars, Vintage Full Body Stock Cars, Hornets | Results | | Henry Bailey (Vintage Full Body Stock Cars) | - | - | - | 6th |
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| 11/27/2021 | Southern Raceway - Milton, FL Deep Southern Shine Run #8 DIRTcar UMP Modifieds, Sportsmans, Vintage Full Body Stock Cars, Hornets, CRUSA Street Stocks, Pure Stock | Results | | Henry Bailey (Vintage Full Body Stock Cars) | 3rd | - | - | 3rd |
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